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dc.contributor.authorAldabbagh, F
dc.contributor.authorBusfield, WK
dc.contributor.authorJenkins, ID
dc.date.accessioned2017-05-03T13:33:34Z
dc.date.available2017-05-03T13:33:34Z
dc.date.issued2001
dc.identifier.issn0004-9425
dc.identifier.doi10.1071/CH01100
dc.identifier.urihttp://hdl.handle.net/10072/3565
dc.description.abstractThe thiyl radicals derived from 2-mercaptoethanol and thiophenol were found to undergo a complex series of reactions with 1,1,3,3-tetramethyl-2,3-dihydroisoindol-2-yloxyl (TMIO). Thus, treatment of 2-mercaptoethanol with di-t-butyl peroxyoxalate (DTBPO) in the presence of TMIO produced two N-S compounds-a sulfoxamide and a sufonamide-not the expected N-O-S adduct. The reaction between thiophenol and TMIO, which proceeded at a reasonable rate in the absence of DTBPO, produced 1,1,3,3-tetramethyl-2,3-dihydroisoindolin and its corresponding phenylsulfoxamide, diphenyl disulfide, phenylsulfinic acid, and 1,1,3,3-tetramethyl-2,3-dihydroisoindol-2-ylphenylsulfonate (the adduct of TMIO and the phenylsulfonyl radical). The mechanism of formation of these products, and the use of TMIO for trapping S-centred radicals, are discussed. A new radical fragmentation process, which appears to be general for aminoxyl adducts of electron-rich systems, is described.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherCSIRO Publishing
dc.publisher.placeAustralia
dc.relation.ispartofpagefrom313
dc.relation.ispartofpageto318
dc.relation.ispartofissue5
dc.relation.ispartofjournalAustralian Journal of Chemistry
dc.relation.ispartofvolume54
dc.subject.fieldofresearchChemical sciences
dc.subject.fieldofresearchcode34
dc.titleThe Reactivity of Sulfur-Centred Radicals towards TMIO (1,1,3,3-Tetramethyl-2,3-dihydroisoindol-2-yloxyl). A New Type of Radical Fragmentation Reaction
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.facultyAn Unassigned Group, An Unassigned Department
gro.date.issued2015-05-21T02:38:01Z
gro.hasfulltextNo Full Text
gro.griffith.authorJenkins, Ian D.
gro.griffith.authorBusfield, Ken K.
gro.griffith.authorAldabbagh, Fawaz


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